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mesoionic compounds

Dipolar five- (possibly six-) membered heterocyclic compounds in which both the negative and the positive charge are delocalized, for which a totally covalent structure cannot be written, and which cannot be represented satisfactorily by any one polar structure. The formal positive charge is associated with the ring atoms, and the formal negative charge is associated with ring atoms or an exocyclic nitrogen or chalcogen atom. Mesoionic compounds are a subclass of betaines.
See also: munchnones, sydnones
PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1349
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8.
Last update: 2014-02-24; version: 2.3.3.
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